A white neoclassical building with columns and a clock tower, surrounded by brick buildings and a clear blue sky.

Search Holiday Rentals in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sep - 6 Sep
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Winchester holiday rentals

Cabin, Private Bathroom (The Pond Cabin) | Exterior

The Pond Cabin

The Pond Cabin
2.0 star property
Linden
The price is 6.284.266 ₫
12.007.155 ₫ total
includes taxes & fees
22 Jul - 23 Jul
The Pond Cabin
Lobby

Roadhaven1830

Roadhaven1830
3.0 star property
Mount Jackson
9.6 out of 10, Exceptional, (43 reviews)
"Very clean close to every and anything local food was amazing and host had a book that showed a lot about the area which came in handy and grounds was so nice games was fun and pit was amazing bed was so comfortable shower pressure was great water was nice an hot too will come back "
United States
Varnell
The price is 2.839.752 ₫
3.189.042 ₫ total
includes taxes & fees
15 Jul - 16 Jul
Roadhaven1830
Cabin, 1 Queen Bed, Mountain View | Pillow-top beds, free WiFi, bed sheets

Canal Cabins

Canal Cabins
3.0 star property
Paw Paw
9.8 out of 10, Exceptional, (16 reviews)
"A great place for a nice getaway. The place is well tailored for the cyclists."
United States
Nebojsa
The price is 3.733.890 ₫
4.219.295 ₫ total
includes taxes & fees
20 Jul - 21 Jul
Canal Cabins
House (3 Bedrooms) | Interior

5 Mi to Harpers Ferry Nhp: Quiet Deck & Garden

5 Mi to Harpers Ferry Nhp: Quiet Deck & Garden
3.0 star property
Harpers Ferry
The price is 4.443.855 ₫
9.825.127 ₫ total
includes taxes & fees
1 Aug - 2 Aug
5 Mi to Harpers Ferry Nhp: Quiet Deck & Garden
Interior

2-Bedroom cabin Hot tub Fireplace PS5

2-Bedroom cabin Hot tub Fireplace PS5
2.0 star property
The Woods
7.0 out of 10, Good, (10 reviews)
"Nice cabin. Could’ve been cleaner outside. Host was nice and surrounding area, beautiful. "
United States
Chris
The price is 3.411.581 ₫
6.508.726 ₫ total
includes taxes & fees
13 Jul - 14 Jul
2-Bedroom cabin Hot tub Fireplace PS5
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Quality Inn Winchester

Quality Inn Winchester

8/10 Good
"The hotel was fine, the staff was friendly and helpful. It was the right hotel for the right price."
Martha 1-night trip
Posted 1 hour ago
Quality Inn Winchester

Frequently asked questions

Can I find holiday rentals in Winchester?

Yes, there are holiday rentals in Winchester close to Shenandoah Valley Discovery Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists like the array of shops and top-notch restaurants in Winchester. You can also check out the theatre scene while you're visiting.

How many holiday rentals will I find in Winchester?

Choose from 14 Expedia holiday rentals in Winchester for a memorable holiday.

What’s there to see and do in Winchester?

Shenandoah Valley Discovery Museum and Rocking S Ranch are a couple of the family-friendly sights, whereas cultural attractions include Winchester Little Theater and Museum of the Shenandoah Valley. Other places in town to visit include Patsy Cline Historic House and Apple Blossom Mall.

What’s a holiday rental in Winchester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winchester. Holiday rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from public hotel lifts and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a family getaway.